You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2020-02-26 21:24:06 UTC
HMDB IDHMDB0002372
Secondary Accession Numbers
  • HMDB02372
Metabolite Identification
Common NameN-Phenylacetylphenylalanine
DescriptionN-Phenylacetylphenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Phenylacetylphenylalanine is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752246
Synonyms
ValueSource
3-Phenyl-N-(phenylacetyl)-alanineHMDB
L-3-Phenyl-N-(phenylacetyl)-alanineHMDB
N-(Phenylacetyl)-L-phenylalanineHMDB
N-Phenylacetyl-L-phenylalanineHMDB
N-Phenylacetylphenylalanine, (D)-isomerHMDB
(2S)-2-[(1-Hydroxy-2-phenylethylidene)amino]-3-phenylpropanoateGenerator
N-PhenylacetylphenylalanineMeSH
Chemical FormulaC17H17NO3
Average Molecular Weight283.3218
Monoisotopic Molecular Weight283.120843415
IUPAC Name(2S)-3-phenyl-2-(2-phenylacetamido)propanoic acid
Traditional NameN-phenylacetyl-L-phenylalanine
CAS Registry Number738-75-0
SMILES
OC(=O)[C@H](CC1=CC=CC=C1)NC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C17H17NO3/c19-16(12-14-9-5-2-6-10-14)18-15(17(20)21)11-13-7-3-1-4-8-13/h1-10,15H,11-12H2,(H,18,19)(H,20,21)/t15-/m0/s1
InChI KeyLIIPHJDKZNTNII-HNNXBMFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPhenylalanine and derivatives
Alternative Parents
Substituents
  • Phenylalanine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • 3-phenylpropanoic-acid
  • Amphetamine or derivatives
  • Phenylacetamide
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP2.39ALOGPS
logP2.73ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.28 m³·mol⁻¹ChemAxon
Polarizability29.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7920000000-414527b0d8767edb022aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9301000000-6bba534fc811e446dd42Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ai-2890000000-731f005addd7e44b2d79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1920000000-1a43b8b4de97159d1462Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-3ae402042e506b3eac68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0490000000-47fac515ba1e5c7e08a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00m3-1940000000-4ac1507005c25d36f8b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9700000000-2bb6f7f95d0c2306716fSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.988 +/- 4.615 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified5.592 +/- 3.046 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022983
KNApSAcK IDNot Available
Chemspider ID43287
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound47579
PDB IDNot Available
ChEBI ID975589
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Burley SK, Wang AH, Votano JR, Rich A: Antigelling and antisickling bisphenyl oligopeptides and peptide analogues have similar structural features. Biochemistry. 1987 Aug 11;26(16):5091-9. [PubMed:3663644 ]
  2. Votano JR, Altman J, Wilchek M, Gorecki M, Rich A: Potential use of biaromatic L-phenylalanyl derivatives as therapeutic agents in the treatment of sickle cell disease. Proc Natl Acad Sci U S A. 1984 May;81(10):3190-4. [PubMed:6587344 ]